WO2017031775A1 - Branched organosilicon material and method for preparing liquid crystal display panel - Google Patents
Branched organosilicon material and method for preparing liquid crystal display panel Download PDFInfo
- Publication number
- WO2017031775A1 WO2017031775A1 PCT/CN2015/088752 CN2015088752W WO2017031775A1 WO 2017031775 A1 WO2017031775 A1 WO 2017031775A1 CN 2015088752 W CN2015088752 W CN 2015088752W WO 2017031775 A1 WO2017031775 A1 WO 2017031775A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substrate
- liquid crystal
- atom
- silicone material
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1334—Constructional arrangements; Manufacturing methods based on polymer dispersed liquid crystals, e.g. microencapsulated liquid crystals
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/133742—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers for homeotropic alignment
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
- G02F1/13378—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation
- G02F1/133788—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by treatment of the surface, e.g. embossing, rubbing or light irradiation by light irradiation, e.g. linearly polarised light photo-polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1341—Filling or closing of cells
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1341—Filling or closing of cells
- G02F1/13415—Drop filling process
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/136—Liquid crystal cells structurally associated with a semi-conducting layer or substrate, e.g. cells forming part of an integrated circuit
- G02F1/1362—Active matrix addressed cells
- G02F1/1368—Active matrix addressed cells in which the switching element is a three-electrode device
Definitions
- the invention relates to the field of liquid crystal display and relates to a branched type silicone material.
- the described silicone material is capable of orienting the LC vertically.
- the invention also relates to the use of the silicone material.
- a film material is provided, the main function of which is to arrange the liquid crystal molecules in a certain direction, which is called an alignment film (common polyimide (PI) material).
- PI common polyimide
- the phase-matching membrane is mainly classified into a friction phase-type PI material and a photo-phase-type PI material.
- the friction phase is liable to cause problems such as dust particles, static electricity, and brush marks to reduce the process yield.
- the optical phase matching material can avoid these problems, the heat resistance and aging resistance are limited due to limited material properties, and the ability to anchor LC molecules is also weak, thereby affecting the quality of the panel.
- the PI material itself has high polarity and high water absorption, storage and transportation are prone to deterioration, resulting in uneven phase distribution, and the PI material is expensive, and the process of film formation on the TFT-LCD is complicated, resulting in panel cost. improve.
- the present invention is intended to provide a new material and method capable of aligning liquid crystal molecules in a TFT-LCD without the PI film, which greatly simplifies the TFT-LCD process and also reduces TFT. - The production cost of LCD.
- the present application provides a branched type silicone material used in a TFT-LCD, which can align liquid crystal molecules in the case of eliminating the PI film, thereby greatly reducing production.
- the cost of the panel is a branched type silicone material used in a TFT-LCD, which can align liquid crystal molecules in the case of eliminating the PI film, thereby greatly reducing production.
- branched silicone material having a molecular formula as shown in Formula I,
- R 1 is directly bonded to a silicon atom
- R 2 is bonded to a silicon atom through an oxygen atom, and adjacent silicon atoms are connected through an oxygen atom
- n is an integer of 2-15
- R 2 is a C 1 -C 5 alkyl group
- the hetero atom comprises a halogen atom, a nitro group, an alkoxy group or the like.
- the silicone material has a structure mainly divided into two parts of a head group A and a tail group B of a plurality of chains.
- A refers to the Si n O 2n+1 portion, mainly a branched structure;
- B refers to two parts of R 1 n R 2 n+2 , that is, a structure of a plurality of branches.
- the silicone branched small molecule material of the present invention combines the characteristics of organic materials and inorganic materials, on the one hand, has low surface tension and low surface energy; on the other hand, because - The bond energy of Si-O- (462 kJ/mol) is higher than the bond energy of -CC- (347 kJ/mol), which increases the temperature resistance and oxidation resistance of the material itself.
- —Si-O- is also a polar anchoring group that can be anchored to other materials.
- the branched silicone material preferably has an integer of from 2 to 10, more preferably an integer of from 2 to 6.
- R 2 is methyl, ethyl or propyl.
- the H atom in the phenylene group or the cycloalkylene group is optionally substituted or unsubstituted with a halogen atom.
- R 3 is hydrogen, methyl or ethyl.
- R 2 is a methyl group, an ethyl group or a propyl group, and R 1 is selected from the group consisting of
- organosilicon materials when n is 2, 3 or 4, are respectively represented by formula II, III or IV:
- the branched silicone material provided according to the present invention has low surface tension and low energy, and has high temperature resistance and oxidation resistance.
- the silicon-oxygen bond contained in the silicone material can interact with other atoms to function as an anchor.
- the branched silicone material according to the present invention can be obtained by subjecting a silicon compound represented by the general formula R 1 Si(OR 2 ) 3 to controlled hydrolysis.
- the silicon compound represented by the above formula R 1 Si(OR 2 ) 3 can be obtained by a method such as condensation.
- the branched silicone material makes the liquid crystal on the surface of the first substrate and the second substrate The surfaces are arranged vertically;
- the amount of the branched silicone material in the mixed solution is 0.1 to 5% by weight.
- the structure of the silicone material is mainly divided into two parts of a head group A and a tail group B of a plurality of chains.
- A refers to the Si n O 2n+1 part, mainly a branched structure, and a plurality of siloxy groups together form a head group, which can enhance the adhesion of the polar group on the surface of the substrate and enhance the anchorage with the substrate. effect.
- the -Si-O- is a polar anchoring group whose primary function is to anchor the head group to the surface of the substrate.
- B refers to two parts of R 1 n R 2 n+2 , that is, a structure of a plurality of branches.
- the main function of the tail group is to vertically align the liquid crystal molecules in a steric hindrance manner.
- the design of multiple tail groups enhances the vertical orientation of the LC molecules.
- the reactive monomer comprises a combination of an epoxy resin and a fatty amine epoxy curing agent, an acrylate and a derivative thereof, and methacrylic acid. At least one of an ester and a derivative thereof and styrene and a derivative thereof.
- the reactive monomer is a radiation-polymerizable compound commonly used in the field of polymers, and will not be described in detail herein.
- the amount of the reactive monomer is from 0.01 to 0.1% by weight.
- the polymerization is radiation polymerization.
- the light source used for the radiation polymerization was UV light at 313 nm.
- the radiation dose is 0.1-1 mW/cm 2 .
- the applied voltage is 15-25 volts.
- the first substrate is a filter film (CF) substrate
- the second substrate is a thin film transistor (TFT) substrate.
- TFT thin film transistor
- the mechanism of action is mainly as follows: 1
- the mechanism of action with ITO is to utilize the lone on the oxygen atom in the -Si-O- An empty p-orbital or d-orbital impurity in the ITO in the ITO of the electron and the substrate surface (extra-core electron arrangement: In:[Kr]4d105s25p1) or tin atom (external electron arrangement: Sn:[Kr]4d105s25p2)
- the combination of the two bonds with SiNx utilizes an oxygen atom in the -Si-O- to interact with the nitrogen atom in the SiNx.
- the branched type silicone material combines the characteristics of an organic material and an inorganic material, has a low surface tension, a low surface energy, and has high temperature resistance and oxidation resistance.
- A has a plurality of -Si-O- groups, which mainly enhance the anchoring action with the substrate.
- the structure of B having a plurality of branches mainly improves the vertical orientation of the LC.
- the PI oriented film in the TFT-LCD is replaced by the branched organic silicon material, the PI segment process is omitted, the preparation process of the liquid crystal panel is greatly simplified, and the panel is reduced. Cost of production.
- a liquid crystal panel comprising: a first substrate, a second substrate, a liquid crystal, a polymer, and the above-described branched silicone material.
- the liquid crystals can be arranged in a certain direction.
- the polymer is a polymer obtained by polymerizing a reactive monomer.
- the liquid crystal of the present invention is a liquid crystal molecule commonly used in the art, and will not be described herein.
- the first substrate is a filter film substrate
- the second substrate is a thin film transistor substrate.
- the first substrate and the second substrate are free of an alignment film.
- a novel branched silicone material having a plurality of siloxy groups and a plurality of branched structures.
- the branched type silicone material when used in the field of LCD, on the one hand, it can form an anchoring action with the substrate, and the effect of a plurality of branches can improve the vertical alignment effect of the liquid crystal LC.
- the branched silicone material provided by the present invention can be used for preparing a liquid crystal panel, and a liquid crystal panel can be produced without an alignment film.
- Figure 1 is a schematic view showing the structure of a branched silicone material according to the present invention.
- FIG. 2 is a schematic view showing the action of a branched silicone material according to an embodiment of the present invention
- FIG. 3 is a process flow diagram of preparing a liquid crystal panel according to an embodiment of the present invention.
- FIG. 4 is a schematic view of a liquid crystal panel in accordance with an embodiment of the present invention.
- FIG. 1 is a schematic view showing the structure of a branched silicone material according to the present invention.
- the structure of the branched type silicone material is mainly divided into two parts of a head group A and a tail group B of a plurality of chains.
- A refers to the Si n O 2n+1 portion, mainly a branched structure;
- B refers to two parts of R 1 n R 2 n+2 , that is, a structure of a plurality of branches.
- the first substrate 1 is a CF substrate
- the second substrate 6 is a TFT substrate.
- Indium tin oxide layers (ITO) 2 and 7 are respectively disposed on the first substrate 1 and the second substrate 6, wherein the ITO only partially covers the second substrate 6.
- ITO Indium tin oxide layers
- the liquid crystal molecules are oriented vertically.
- the silicone material 5 functions as a vertical alignment agent.
- FIG. 3 is a process flow diagram of preparing a liquid crystal panel in accordance with one embodiment of the present invention. a) providing a casing including the first substrate 1 and the second substrate 6, both of which do not contain an alignment film; and the reactive monomer 4 and the branched silicone material 5 are added Into the liquid crystal 3, a mixed solution is prepared; the mixed solution is dropped between the first substrate 1 and the second substrate 6 in the casing, and at this time, the branched silicone material 5 makes liquid crystal 3 is vertically arranged on the surface of the first substrate 1 and the surface of the second substrate 6. b) Applying a voltage of 20 V causes the liquid crystal to deflect.
- the reaction type monomer 4 is polymerized on the surface of the first substrate 1 and the surface of the second substrate 6 under irradiation of UV light at 313 nm (0.5 mW/cm 2 ) to obtain a polymer 9, and the resulting polymerization is carried out.
- the object 9 anchors the liquid crystal.
- the liquid crystal 3 in the panel has a pretilt angle 8.
- the reactive monomer used is methyl acrylate.
- the amount of the reactive monomer used was 0.05% by weight, and the amount of the branched silicone material was 3% by weight.
- n 3
- R 2 is a methyl group.
- Fig. 4 shows a liquid crystal panel obtained according to the present invention, in which the liquid crystal molecules are arranged normally and the picture can be normally displayed. This shows that the branched type silicone material can vertically align liquid crystal molecules, and a liquid crystal panel can be obtained without using an alignment film.
- silicone materials The synthesis of two silicone materials is exemplified below, and other silicone materials can also be synthesized by the following methods.
- the molar ratio of the compound of the formula i and the compound of the formula ii is 1:1 to 1:1.4, preferably 1:1.2; the compound of the formula i and the formula ii
- the reaction temperature of the compound is from 20 ° C to 60 ° C, preferably 50 ° C, and the reaction time is from 1 h to 5 h, preferably 4 h.
- the reaction temperature of the compound of the formula iii with the pentylamine compound of the formula iv is from 60 ° C to 90 ° C, preferably 80 ° C; and the reaction is carried out for 1 h to 5 h, preferably 3 h.
- R 1 is R 2 is a methyl group, that is, It is a compound represented by the formula iv.
- H 1 -NMR data are as follows: ⁇ : 0.96 (6H), 1.33 (4H), 1.29 (8H), 1.59 (4H), 3.20 (4H), 8.0 (4H), 8.13 (4H), 7.69 (4H), 3.55 (12H), 3.2 (4H), 0.88 (4H).
- the molar ratio of the compound of the formula i to the compound of the formula v is from 1:1 to 1:1.4, preferably 1:1.2; the reaction temperature of the compound of the formula i and the compound of the formula v is from 20 to 60 ° C, preferably 40 °C, the reaction time is 1h-5h, preferably 3h.
- the molar ratio of the compound represented by the formula vi to n-octanol was 1:1, and 1.1 times of SOCl2 was further added thereto, and the reaction was carried out for 1 hour.
- a silicone material having n of 2 is prepared, and the molar ratio of the two reactants is from 1:1.1 to 1.5, preferably 1:1.2.
- the reaction temperature was 50 ° C and a small amount of H 2 SO 4 was added to promote hydrolysis.
- H 1 -NMR data are as follows: ⁇ : 0.96 (6H), 1.33 (4H), 1.29 (16H), 1.57 (4H), 4.15 (4H), 3.55 (12H), 1.93 (12H), 8.0 (2H), 3.0 (4H), 0.84 (4H).
Abstract
Description
Claims (16)
- 一种支化型有机硅材料,其分子式如式I所示,A branched type silicone material having a molecular formula as shown in Formula I,SinO2n+1R1 nR2 n+2, 式ISi n O 2n+1 R 1 n R 2 n+2 , Formula I其中,R1与硅原子直接相连,R2通过氧原子与硅原子相连,相邻的硅原子通过氧原子相连;n为2-15的整数,R2为C1-C5的烷基,R1为含10-30碳原子的基团,且R1基团任选地包含或不包含选自-CR3=CR3-、-C≡C-、C6-C20亚芳基、C3-C15亚环烷基、-CONH-和-COO-的基团,且R1基团中的一个或多个H原子任选地被杂原子取代或不取代,R3为氢或C1-C3的烷基。Wherein R 1 is directly bonded to a silicon atom, R 2 is bonded to a silicon atom through an oxygen atom, and adjacent silicon atoms are connected through an oxygen atom; n is an integer of 2-15, and R 2 is a C 1 -C 5 alkyl group; R 1 is a group having 10 to 30 carbon atoms, and the R 1 group optionally contains or does not include a -CR 3 =CR 3 -, -C≡C-, C 6 -C 20 arylene group, a C 3 -C 15 cycloalkylene group, a -CONH- and -COO- group, and one or more H atoms in the R 1 group are optionally substituted or unsubstituted by a hetero atom, and R 3 is hydrogen or C 1 -C 3 alkyl group.
- 根据权利要求1所述的支化型有机硅材料,其中,n为2-10的整数;和/或,R2为甲基、乙基或丙基;和/或,R1基团中包含选自-CR3=CR3-、-C≡C-、亚苯基、C3-C6亚环烷基、-CONH-和-COO-的基团,且所述亚苯基或亚环烷基中的H原子任选地被卤素原子取代或不取代,R3为氢、甲基或乙基。The branched silicone material according to claim 1, wherein n is an integer of 2 to 10; and/or R 2 is a methyl group, an ethyl group or a propyl group; and/or the R 1 group is contained a group selected from the group consisting of -CR 3 =CR 3 -, -C≡C-, phenylene, C 3 -C 6 cycloalkylene, -CONH-, and -COO-, and the phenylene or subring The H atom in the alkyl group is optionally substituted or unsubstituted with a halogen atom, and R 3 is hydrogen, methyl or ethyl.
- 一种制备液晶面板的方法,包括以下步骤:A method of preparing a liquid crystal panel, comprising the steps of:1)设置包含第一基板和第二基板的盒体,所述第一基板和第二基板上均不含配向膜;1) providing a casing including a first substrate and a second substrate, wherein the first substrate and the second substrate do not contain an alignment film;2)将反应型单体和支化型有机硅材料加入到液晶中,制得混合溶液;2) adding a reactive monomer and a branched silicone material to the liquid crystal to prepare a mixed solution;3)将所述的混合溶液滴加到所述盒体内的第一基板和第二基板之间,此时,所述支化型有机硅材料使液晶在第一基板的表面以及第二基板的表面垂直排列;3) dropping the mixed solution between the first substrate and the second substrate in the casing, at this time, the branched silicone material makes the liquid crystal on the surface of the first substrate and the second substrate The surfaces are arranged vertically;4)施加电压使液晶发生偏转,然后使反应型单体在所述第一基板的表面和第二基板的表面聚合,锚定液晶;4) applying a voltage to deflect the liquid crystal, and then polymerizing the reactive monomer on the surface of the first substrate and the surface of the second substrate to anchor the liquid crystal;5)释放电压,得到所述液晶面板;5) releasing a voltage to obtain the liquid crystal panel;其中,所述支化型有机硅材料的分子式如式I所示,Wherein, the molecular formula of the branched silicone material is as shown in Formula I,SinO2n+1R1 nR2 n+2, 式ISi n O 2n+1 R 1 n R 2 n+2 , Formula I其中,R1与硅原子直接相连,R2通过氧原子与硅原子相连,相邻的硅原子通过氧原子相连;n为2-15的整数,R2为C1-C5的烷基,R1为含10-30碳原子的基团,且R1基团任选地包含或不包含选自-CR3=CR3-、-C≡C-、C6-C20亚芳基、C3-C15亚环烷基、-CONH-和-COO-的基团,且R1基团中的一个或多个H原子任选地被杂原子取代或不取代,R3为氢或C1-C3的烷基。Wherein R 1 is directly bonded to a silicon atom, R 2 is bonded to a silicon atom through an oxygen atom, and adjacent silicon atoms are connected through an oxygen atom; n is an integer of 2-15, and R 2 is a C 1 -C 5 alkyl group; R 1 is a group having 10 to 30 carbon atoms, and the R 1 group optionally contains or does not include a -CR 3 =CR 3 -, -C≡C-, C 6 -C 20 arylene group, a C 3 -C 15 cycloalkylene group, a -CONH- and -COO- group, and one or more H atoms in the R 1 group are optionally substituted or unsubstituted by a hetero atom, and R 3 is hydrogen or C 1 -C 3 alkyl group.
- 根据权利要求5所述的方法,其中,在步骤2)中,所述混合溶液中,所述支化型有机硅材料的量为0.1-5wt%。The method according to claim 5, wherein in the step 2), the amount of the branched silicone material in the mixed solution is from 0.1 to 5% by weight.
- 根据权利要求5所述的方法,其中,在步骤2)中,所述反应型单体包括环氧树脂与脂肪胺类环氧固化剂的组合、丙烯酸酯及其衍生物、甲基丙烯酸酯及其衍生物和苯乙烯及其衍生物中的至少一种;和/或,所述混合溶液中,所述反应型单体的量为0.01-0.1wt%。The method according to claim 5, wherein in the step 2), the reactive monomer comprises a combination of an epoxy resin and a fatty amine epoxy curing agent, an acrylate and a derivative thereof, a methacrylate, and And a derivative thereof and at least one of styrene and a derivative thereof; and/or, in the mixed solution, the reactive monomer is in an amount of 0.01 to 0.1% by weight.
- 根据权利要求5所述的方法,其中,在步骤4)中,所述聚合为辐射聚合,和/或所述施加的电压为15-25v。 The method of claim 5 wherein in step 4) the polymerization is radiation polymerization and/or the applied voltage is 15-25 volts.
- 根据权利要求5所述的方法,其中,在所述1)中,所述第一基板为滤光膜基板,所述第二基板为薄膜三极管基板。The method according to claim 5, wherein in the 1), the first substrate is a filter film substrate, and the second substrate is a thin film transistor substrate.
- 根据权利要求5所述的方法,其中,n为2-10的整数;和/或,R2为甲基、乙基或丙基;和/或,R1基团中包含选自-CR3=CR3-、-C≡C-、亚苯基、C3-C6亚环烷基、-CONH-和-COO-的基团,且所述亚苯基或亚环烷基中的H原子任选地被卤素原子取代或不取代,R3为氢、甲基或乙基。The method according to claim 5, wherein n is an integer from 2 to 10; and/or R 2 is a methyl group, an ethyl group or a propyl group; and/or the R 1 group comprises a group selected from -CR 3 a group of =CR 3 -, -C≡C-, phenylene, C 3 -C 6 cycloalkylene, -CONH- and -COO-, and H in the phenylene or cycloalkylene group The atom is optionally substituted or unsubstituted with a halogen atom, and R 3 is hydrogen, methyl or ethyl.
- 一种液晶面板,包含:第一基板,第二基板,液晶,聚合物以及支化型有机硅材料,所述支化型有机硅材料的分子式如式I所示,A liquid crystal panel comprising: a first substrate, a second substrate, a liquid crystal, a polymer, and a branched silicone material. The molecular formula of the branched silicone material is as shown in Formula I,SinO2n+1R1 nR2 n+2, 式I Si n O 2n+1 R 1 n R 2 n+2 , Formula I其中,R1与硅原子直接相连,R2通过氧原子与硅原子相连,相邻的硅原子通过氧原子相连;n为2-15的整数,R2为C1-C5的烷基,R1为含10-30碳原子的基团,且R1基团任选地包含或不包含选自-CR3=CR3-、-C≡C-、C6-C20亚芳基、C3-C15亚环烷基、-CONH-和-COO-的基团,且R1基团中的一个或多个H原子任选地被杂原子取代或不取代,R3为氢或C1-C3的烷基。Wherein R 1 is directly bonded to a silicon atom, R 2 is bonded to a silicon atom through an oxygen atom, and adjacent silicon atoms are connected through an oxygen atom; n is an integer of 2-15, and R 2 is a C 1 -C 5 alkyl group; R 1 is a group having 10 to 30 carbon atoms, and the R 1 group optionally contains or does not include a -CR 3 =CR 3 -, -C≡C-, C 6 -C 20 arylene group, a C 3 -C 15 cycloalkylene group, a -CONH- and -COO- group, and one or more H atoms in the R 1 group are optionally substituted or unsubstituted by a hetero atom, and R 3 is hydrogen or C 1 -C 3 alkyl group.
- 根据权利要求13所述的液晶面板,其中,n为2-10的整数;和/或,R2为甲基、乙基或丙基;和/或,R1基团中包含选自-CR3=CR3-、-C≡C-、亚苯基、C3-C6亚环烷基、-CONH-和-COO-的基团,且所述亚苯基或亚环烷基中的H原子任选地被卤素原子取代或不取代,R3为氢、甲基或乙基。The liquid crystal panel according to claim 13, wherein n is an integer of 2 to 10; and/or R 2 is a methyl group, an ethyl group or a propyl group; and/or the R 1 group contains a group selected from -CR a group of 3 =CR 3 -, -C≡C-, phenylene, C 3 -C 6 cycloalkylene, -CONH- and -COO-, and in the phenylene or cycloalkylene group The H atom is optionally substituted or unsubstituted with a halogen atom, and R 3 is hydrogen, methyl or ethyl.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2018109278A RU2683825C1 (en) | 2015-08-25 | 2015-09-01 | Branched organosilicon polymer and a method of making liquid crystal display panels for information display |
US14/897,783 US10377950B2 (en) | 2015-08-25 | 2015-09-01 | Branched organosilicon material, and method for manufacturing liquid crystal display panels |
JP2018510119A JP6661752B2 (en) | 2015-08-25 | 2015-09-01 | Branched organic silicon material and method for manufacturing liquid crystal panel |
KR1020187007583A KR102154414B1 (en) | 2015-08-25 | 2015-09-01 | Branch-type organosilicon material and manufacturing method of liquid crystal panel |
GB1802219.4A GB2556587B (en) | 2015-08-25 | 2015-09-01 | A branched organosilicon material, and method for manufacturing liquid crystal display panels |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510526256.0A CN105061489B (en) | 2015-08-25 | 2015-08-25 | A kind of branching type organosilicon material and the method for preparing liquid crystal display panel |
CN201510526256.0 | 2015-08-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017031775A1 true WO2017031775A1 (en) | 2017-03-02 |
Family
ID=54491049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2015/088752 WO2017031775A1 (en) | 2015-08-25 | 2015-09-01 | Branched organosilicon material and method for preparing liquid crystal display panel |
Country Status (7)
Country | Link |
---|---|
US (1) | US10377950B2 (en) |
JP (1) | JP6661752B2 (en) |
KR (1) | KR102154414B1 (en) |
CN (1) | CN105061489B (en) |
GB (1) | GB2556587B (en) |
RU (1) | RU2683825C1 (en) |
WO (1) | WO2017031775A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108474982B (en) * | 2016-01-07 | 2021-11-02 | 夏普株式会社 | Liquid crystal display device and method for manufacturing liquid crystal display device |
CN110187565B (en) * | 2019-05-23 | 2021-11-02 | Tcl华星光电技术有限公司 | Display and method of manufacturing the same |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2915803B2 (en) * | 1994-07-22 | 1999-07-05 | 昭和高分子株式会社 | Water-based water-repellent and waterproof coating agent |
JP2005097150A (en) * | 2003-09-24 | 2005-04-14 | Kao Corp | Hair cleanser composition |
JP2006131850A (en) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | Thermosetting composition |
CN102007447A (en) * | 2008-04-18 | 2011-04-06 | 积水化学工业株式会社 | Sealing agent for use in liquid crystal dropping process, sealing agent for liquid crystal panel, vertical-conduction material, and liquid crystal display element |
CN102516916A (en) * | 2011-12-12 | 2012-06-27 | 东莞市派乐玛新材料技术开发有限公司 | Liquid crystal sealant composition |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3574670A (en) * | 1968-07-12 | 1971-04-13 | Texas Instruments Inc | Method of coating a suction box cover with an organodisiloxane |
EP0664452B1 (en) | 1994-01-19 | 2002-07-31 | Roche Diagnostics GmbH | Biotin-silane compounds and binding matrix containing these compounds |
DE4435728A1 (en) * | 1994-01-19 | 1995-07-20 | Boehringer Mannheim Gmbh | Biotin silane compounds and binding matrix containing these compounds |
RU2177484C1 (en) * | 2000-05-31 | 2001-12-27 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт химии и технологии элементоорганических соединений" | Oligodiethylethyloctylsiloxanes of branched structure and method of their synthesis |
JP2006308724A (en) * | 2005-04-27 | 2006-11-09 | Sony Corp | Optical compensating sheet and method for manufacturing the same, polarizing sheet, and liquid crystal display device |
JP2008053631A (en) * | 2006-08-28 | 2008-03-06 | Toyota Motor Corp | Organic thin film having electrochemical activity, method of manufacturing the same, and device using the same |
BRPI0924220A2 (en) | 2009-03-13 | 2016-01-26 | Sharp Kk | liquid crystal display device and method for manufacturing it |
BR112014007926A2 (en) | 2011-10-03 | 2017-04-11 | Rolic Ag | alignment photo materials |
JP2015099170A (en) * | 2012-03-05 | 2015-05-28 | シャープ株式会社 | Liquid crystal display device and method for manufacturing liquid crystal display device |
JP2014028788A (en) | 2012-06-29 | 2014-02-13 | Shikoku Chem Corp | Imidazole silane compound, synthesizing method for the compound, and use thereof |
KR102018163B1 (en) * | 2013-02-07 | 2019-09-04 | 제이에스알 가부시끼가이샤 | Liquid crystal aligning agent, liquid crystal alignment film, and liquid crystal display device and menufacturing method thereof |
JP6093222B2 (en) | 2013-03-29 | 2017-03-08 | Dowaメタルテック株式会社 | Electroplating method and mask member used therefor |
KR102344233B1 (en) * | 2013-06-06 | 2021-12-27 | 닛산 가가쿠 가부시키가이샤 | Liquid crystal aligning agent, liquid crystal alignment film and liquid crystal display element |
JP2018510119A (en) | 2015-03-30 | 2018-04-12 | ダウ グローバル テクノロジーズ エルエルシー | Modified cellulose ethers with improved workability for use in gypsum smoothing mortar and joint material applications |
-
2015
- 2015-08-25 CN CN201510526256.0A patent/CN105061489B/en active Active
- 2015-09-01 KR KR1020187007583A patent/KR102154414B1/en active IP Right Grant
- 2015-09-01 JP JP2018510119A patent/JP6661752B2/en active Active
- 2015-09-01 GB GB1802219.4A patent/GB2556587B/en active Active
- 2015-09-01 WO PCT/CN2015/088752 patent/WO2017031775A1/en active Application Filing
- 2015-09-01 RU RU2018109278A patent/RU2683825C1/en active
- 2015-09-01 US US14/897,783 patent/US10377950B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2915803B2 (en) * | 1994-07-22 | 1999-07-05 | 昭和高分子株式会社 | Water-based water-repellent and waterproof coating agent |
JP2005097150A (en) * | 2003-09-24 | 2005-04-14 | Kao Corp | Hair cleanser composition |
JP2006131850A (en) * | 2004-11-09 | 2006-05-25 | Toagosei Co Ltd | Thermosetting composition |
CN102007447A (en) * | 2008-04-18 | 2011-04-06 | 积水化学工业株式会社 | Sealing agent for use in liquid crystal dropping process, sealing agent for liquid crystal panel, vertical-conduction material, and liquid crystal display element |
CN102516916A (en) * | 2011-12-12 | 2012-06-27 | 东莞市派乐玛新材料技术开发有限公司 | Liquid crystal sealant composition |
Also Published As
Publication number | Publication date |
---|---|
JP2018532697A (en) | 2018-11-08 |
US20180057745A1 (en) | 2018-03-01 |
US10377950B2 (en) | 2019-08-13 |
RU2683825C1 (en) | 2019-04-02 |
KR102154414B1 (en) | 2020-09-09 |
GB2556587A (en) | 2018-05-30 |
CN105061489A (en) | 2015-11-18 |
GB2556587B (en) | 2020-09-02 |
JP6661752B2 (en) | 2020-03-11 |
CN105061489B (en) | 2019-03-05 |
GB201802219D0 (en) | 2018-03-28 |
KR20180041722A (en) | 2018-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6586438B2 (en) | Polymer suitable for highly efficient liquid crystal alignment film using light | |
WO2018120325A1 (en) | Vertical aligning agent material | |
US10690966B2 (en) | Material of alignment films, methods of fabricating liquid crystal display panels and liquid crystal display panels | |
US9677003B2 (en) | Liquid crystal display device and method for producing the same | |
US9139775B2 (en) | Liquid crystal medium composition for use in liquid crystal display | |
WO2017181466A1 (en) | Liquid crystal material, liquid crystal display panel manufacturing method, and liquid crystal display panel | |
US9261733B2 (en) | Liquid crystal display device and method for producing the same | |
WO2017084154A1 (en) | Reaction-type vertical alignment material, liquid crystal display panel, and liquid crystal alignment method | |
US20130287970A1 (en) | Liquid Crystal Medium Composition and Liquid Crystal Display Using Same | |
US9250476B2 (en) | Liquid crystal display device and method for producing the same | |
US20160230096A1 (en) | Liquid crystal display device and method for manufacturing the same | |
TWI706028B (en) | Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element | |
JP6523169B2 (en) | Polymer, polymer composition and liquid crystal alignment film for horizontal electric field drive type liquid crystal display device | |
WO2017084147A1 (en) | Reaction-type vertical alignment organosilicon material and method for manufacturing liquid crystal display panel | |
US10303001B2 (en) | Thermal crosslink material, manufacture method of liquid crystal display panel and liquid crystal display panel | |
JP2013109151A (en) | Liquid crystal aligning agent | |
WO2017031775A1 (en) | Branched organosilicon material and method for preparing liquid crystal display panel | |
US20170090252A1 (en) | Liquid crystal horizontal orientation agent, horizontal orientation type liquid crystal composition, and horizontal orientation type liquid crystal display device and method of fabricating the same | |
KR102466047B1 (en) | Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element | |
WO2018074546A1 (en) | Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal element, and polymer | |
JP2015206919A (en) | Manufacturing method of liquid crystal display element, liquid crystal alignment agent, and liquid crystal alignment film | |
WO2014043952A1 (en) | Liquid crystal medium mixture and liquid crystal display using liquid crystal medium mixture | |
JP2019056723A (en) | Liquid crystal display device |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 15902046 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14897783 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 201802219 Country of ref document: GB Kind code of ref document: A Free format text: PCT FILING DATE = 20150901 |
|
ENP | Entry into the national phase |
Ref document number: 2018510119 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2018109278 Country of ref document: RU |
|
ENP | Entry into the national phase |
Ref document number: 20187007583 Country of ref document: KR Kind code of ref document: A |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 15902046 Country of ref document: EP Kind code of ref document: A1 |